# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Roger Davey' 'G. Dent' 'S. Parveen' _publ_contact_author_name 'Prof Roger Davey' _publ_contact_author_address ; School of chemical Engineering and Analytic Sciences University of Manchester PO 88 Sackville Street Manchester M601QD ; _publ_contact_author_email ROGER.DAVEY@MANCHESTER.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Linking solution chemistry to crystal nucleation:the case of tetrolic acid ; _publ_requested_category FO data_r _database_code_depnum_ccdc_archive 'CCDC 258387' _audit_creation_date 2004-11-19T14:56:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H16 O6' _chemical_formula_sum 'C12 H16 O6' _chemical_formula_weight 256.25 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.1673(2) _cell_length_b 6.5063(4) _cell_length_c 12.4424(6) _cell_angle_alpha 97.557(3) _cell_angle_beta 92.948(3) _cell_angle_gamma 91.670(2) _cell_volume 333.77(3) _cell_formula_units_Z 1 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3232 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 25.35 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 136 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.994 _exptl_absorpt_correction_T_max 1.009 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.105133 _diffrn_orient_matrix_ub_12 -0.165599E-1 _diffrn_orient_matrix_ub_13 -0.748594E-1 _diffrn_orient_matrix_ub_21 0.164645 _diffrn_orient_matrix_ub_22 0.986285E-1 _diffrn_orient_matrix_ub_23 -0.222701E-1 _diffrn_orient_matrix_ub_31 0.14018 _diffrn_orient_matrix_ub_32 -0.118611 _diffrn_orient_matrix_ub_33 -0.222197E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_unetI/netI 0.0432 _diffrn_reflns_number 4154 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.3 _diffrn_reflns_theta_full 25.3 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 1189 _reflns_number_gt 976 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.0435P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1189 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.127 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.03 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3 O 0.8480(2) 0.36219(13) 0.06023(7) 0.0451(3) Uani 1 1 d . . . O2 O 0.5543(3) 0.32792(16) 0.30252(9) 0.0719(4) Uani 1 1 d . . . O1 O 0.5894(3) 0.07759(16) 0.16558(8) 0.0571(4) Uani 1 1 d . . . C3 C 0.2578(3) -0.1333(2) 0.37072(10) 0.0444(4) Uani 1 1 d . . . C5 C 0.9956(4) 0.5545(2) 0.11253(10) 0.0442(4) Uani 1 1 d . . . C2 C 0.3725(3) -0.0084(2) 0.32089(10) 0.0449(4) Uani 1 1 d . . . C6 C 1.0101(4) 0.2876(2) -0.03561(11) 0.0429(4) Uani 1 1 d . . . C1 C 0.5125(3) 0.1499(2) 0.26422(10) 0.0420(4) Uani 1 1 d . . . C4 C 0.1184(5) -0.2869(3) 0.43175(14) 0.0542(4) Uani 1 1 d . . . H5A H 1.221(4) 0.529(2) 0.1370(12) 0.052(4) Uiso 1 1 d . . . H6B H 0.889(4) 0.160(2) -0.0696(12) 0.054(4) Uiso 1 1 d . . . H6A H 1.236(4) 0.258(2) -0.0150(11) 0.046(4) Uiso 1 1 d . . . H5B H 0.874(4) 0.596(2) 0.1734(13) 0.052(4) Uiso 1 1 d . . . H1 H 0.683(5) 0.183(3) 0.1340(17) 0.093(6) Uiso 1 1 d . . . H4A H -0.096(9) -0.339(6) 0.402(3) 0.056(9) Uiso 0.5 1 d P . . H4B H -0.054(8) -0.219(5) 0.479(3) 0.046(8) Uiso 0.5 1 d P . . H4C H 0.290(8) -0.323(5) 0.487(3) 0.046(8) Uiso 0.5 1 d P . . H4D H 0.273(12) -0.404(7) 0.425(4) 0.088(13) Uiso 0.5 1 d P . . H4E H 0.129(10) -0.239(5) 0.507(3) 0.055(9) Uiso 0.5 1 d P . . H4F H 0.078(10) -0.423(6) 0.385(3) 0.056(9) Uiso 0.5 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0537(6) 0.0419(6) 0.0400(6) 0.0072(4) 0.0088(4) -0.0114(4) O2 0.1158(11) 0.0410(6) 0.0579(7) 0.0014(5) 0.0190(6) -0.0131(6) O1 0.0854(8) 0.0409(6) 0.0456(6) 0.0055(4) 0.0195(5) -0.0132(5) C3 0.0510(8) 0.0431(7) 0.0392(7) 0.0061(6) 0.0040(6) -0.0021(6) C5 0.0501(9) 0.0460(8) 0.0352(7) 0.0025(6) 0.0045(6) -0.0089(6) C2 0.0531(9) 0.0429(7) 0.0389(7) 0.0066(6) 0.0040(6) -0.0023(6) C6 0.0461(8) 0.0375(7) 0.0441(7) 0.0018(6) 0.0049(6) -0.0034(6) C1 0.0492(8) 0.0377(7) 0.0394(7) 0.0070(5) 0.0010(5) -0.0018(6) C4 0.0671(12) 0.0501(9) 0.0473(9) 0.0136(7) 0.0105(8) -0.0090(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C6 1.4366(16) . ? O3 C5 1.4377(16) . ? O2 C1 1.1975(16) . ? O1 C1 1.3143(17) . ? O1 H1 0.92(2) . ? C3 C2 1.1889(19) . ? C3 C4 1.4572(19) . ? C5 C6 1.4932(19) 2_765 ? C5 H5A 0.999(16) . ? C5 H5B 0.947(17) . ? C2 C1 1.4481(18) . ? C6 C5 1.4932(19) 2_765 ? C6 H6B 0.993(16) . ? C6 H6A 0.993(15) . ? C4 H4A 0.98(4) . ? C4 H4B 1.03(3) . ? C4 H4C 1.02(3) . ? C4 H4D 1.01(5) . ? C4 H4E 0.95(4) . ? C4 H4F 1.00(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O3 C5 110.70(10) . . ? C1 O1 H1 109.4(13) . . ? C2 C3 C4 179.76(17) . . ? O3 C5 C6 109.90(11) . 2_765 ? O3 C5 H5A 108.6(8) . . ? C6 C5 H5A 110.8(9) 2_765 . ? O3 C5 H5B 106.2(9) . . ? C6 C5 H5B 111.2(9) 2_765 . ? H5A C5 H5B 110.0(12) . . ? C3 C2 C1 177.63(14) . . ? O3 C6 C5 110.12(11) . 2_765 ? O3 C6 H6B 106.5(9) . . ? C5 C6 H6B 109.6(8) 2_765 . ? O3 C6 H6A 109.5(8) . . ? C5 C6 H6A 109.9(8) 2_765 . ? H6B C6 H6A 111.3(12) . . ? O2 C1 O1 123.25(12) . . ? O2 C1 C2 123.95(12) . . ? O1 C1 C2 112.80(11) . . ? C3 C4 H4A 112.5(18) . . ? C3 C4 H4B 109.1(16) . . ? H4A C4 H4B 70(2) . . ? C3 C4 H4C 108.2(17) . . ? H4A C4 H4C 138(2) . . ? H4B C4 H4C 104(2) . . ? C3 C4 H4D 104(2) . . ? H4A C4 H4D 110(3) . . ? H4B C4 H4D 143(3) . . ? H4C C4 H4D 51(3) . . ? C3 C4 H4E 111(2) . . ? H4A C4 H4E 115(3) . . ? H4B C4 H4E 51(2) . . ? H4C C4 H4E 54(2) . . ? H4D C4 H4E 104(3) . . ? C3 C4 H4F 111.0(19) . . ? H4A C4 H4F 57(2) . . ? H4B C4 H4F 122(3) . . ? H4C C4 H4F 102(3) . . ? H4D C4 H4F 55(3) . . ? H4E C4 H4F 136(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O3 C5 C6 58.14(16) . . . 2_765 ? C4 C3 C2 C1 -11E1(4) . . . . ? C5 O3 C6 C5 -58.27(16) . . . 2_765 ? C3 C2 C1 O2 -7(4) . . . . ? C3 C2 C1 O1 173(4) . . . . ?